Ruyi Li, Huaqin Wu, Hang Liu, Junjie Bai, Zao Zhang, Muyang Zhu, Pengcheng Lian and Xiaobing Wan
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Modular construction of sulfinimidate esters: expanding chemical space and enabling late-stage diversification†
Sulfinimidate esters, despite their distinctive structural and biological properties, remain underexplored, primarily due to the paucity of information concerning their synthetic methodologies and structural diversity. Herein, we present a pioneering synthetic strategy for sulfinimidate esters that harnesses commercially available feedstock chemicals. The cornerstone of this modular approach lies in the employment of thiols as essential linchpins, facilitating oxidative coupling reactions with amines and alcohols. This methodology has facilitated the synthesis of an extensive array of sulfinimidate esters, showcasing a diverse collection that encompasses more than 150 distinct examples, notably featuring over 20 heterocyclic and carbocyclic variants. The versatility of this synthetic protocol is underscored by successful scale-up attempts and its application to the late-stage modification of intricate molecules. Consequently, our research not only advances the understanding of sulfinimidate esters by providing a robust synthetic pathway but also holds the potential to accelerate the assembly of molecule libraries for drug discovery.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.